Diethyl Oxalate → HCID 14064733, compound

HRID 1051346Notes

Reaction equation

HRID 1051346 reaction equation
[Na].[O-]CC.[Na+].[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]=1[CH3:16].[C:17](OCC)(=[O:23])[C:18]([O:20]CC)=[O:19]>CCO.O>[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]=1[CH2:16][C:17](=[O:23])[C:18]([OH:20])=[O:19]

Participants

7

Reactant 4

HCID 7268Diethyl OxalateHCID 698542-Fluoro-6-nitrotolueneHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 14064733HCID 14064733, compoundYield 21.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Sodium (2.30 g, 100 mmol) was added to anhydrous EtOH (80 mL) at 0-5° C. for 10 min to prepare a fresh sodium ethoxide solution. A solution of 1-fluoro-2-methyl-3-nitrobenzene (14.4 g, 93.0 mmol) and diethyl oxalate (15.3 g, 105 mmol) in EtOH (80 mL) was added to the above solution, and the resulting mixture was then refluxed for 45 min. After cooling down, the red dark solution was diluted with water (100 mL). After removal of the ethanol, the residue was extracted with EtOAc. The aqueous layer was acidified with 2N HCl to pH around 3 to 4, and extracted with DCM. The organic layers were washed with water, dried, and concentrated to afford 4.5 g (21%) of 3-(2-fluoro-6-nitrophenyl)-2-oxopropanoic acid (32) as red oil. LCMS (ESI) m/z: 245.1 [M+NH4]+.

Workup

  1. temperaturethe resulting mixture was then refluxed for 45 min
  2. temperatureAfter cooling down
  3. customAfter removal of the ethanol
  4. extractionthe residue was extracted with EtOAc
  5. extractionextracted with DCM
  6. washThe organic layers were washed with water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-81b58c9db2414a5b80fd52d046a4c054
Source dataset
uspto-grants-2016_07
Patent number
US09388171B2

Reaction notes

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